The absolute best I had in a Microsoft product was this (paraphrasing): "An error happened because your computer may be turned off". I still have a screenshot of that somewhere. What it meant was that an hypothetical computer I may be trying to connect to (which I wasn't, it was all local) was off, but that wasn't the case. This was seriously WTF.
The second most beautiful one from another Microsoft product was whatever software generating a password and asking me, in a pop-up window, to write it down. The problem was the password was something like:
9mZOvy9E(4)?6b(w(<$KcTU%>9T6cz0Z4YxgQ-<tw035X6S.dLE0[2n0"42`/S=S1{q5{)61s190':&6UHT.4hZXjO6b%l#X7v]~4tIT2Y0._ebFH,>2:G>%*P]7n4"
I probably also still have a screenshot of that somewhere.Haven't used Microsoft stuff in two decades so it was a long time ago. But it's still seriously WTF.